This article in the New York Times Magazine (link >>>) reports on the particular troubles of running commercial air transportation in the failed state of Somalia. The reality faced by intrepid entrepreneurs in that lawless region can easily be transferred to a Traveller contest, with similar aerospace services in an Amber Zone planetary system. Reality is frequently the best source of inspiration. Pay particular heed to the description of the bureaucratic hassles surrounding flight permits, airplane registration and staffing. The adventurous chaps piloting these craft resemble a few characters in my old Traveller campaign.
There is also an old blog post on equally adventurous bush pilots in the Andes here >>>